


Jail Broken

by striderous



Series: A Deal Struck, an Inmate Fucked [1]
Category: Superjail!
Genre: Anal Fingering, Anal Sex, Dom/sub Undertones, Gang Rape, Horny Warden is horny, M/M, Prison Sex, Shower Sex, Stingray is an alien too, Stingray wears STRIPPER HEELS, Tentacle Dick, Those who cheat get their ass BEAT, but not really
Language: English
Status: Completed
Published: 2017-07-15
Updated: 2017-07-15
Packaged: 2018-12-02 09:38:07
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 4,302
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11506698
Author URL: https://archiveofourown.org/users/striderous/pseuds/striderous
Summary: Lord Stingray gets caught cheating on Poker Night, which leads to a rough time with some other inmates. After watching what goes down, the Warden decides to strike up a deal.





	Jail Broken

**Author's Note:**

> This is gonna be a series, depending on whether or not I get good feedback. Or any feedback, really. This fandom is dead af.

It was near the middle of the night when The Warden was awakened by a persistent tapping on his bedroom door. 

“’Tis some visitor,” He muttered, “tapping at my chamber doo-” His sentence was cut off by Jared barging into the room, waving his stubby arms in the air. 

“Sir! Sir! We have a code pink!” The short man yelled frantically, sweat accumulating on his enlarged forehead. The Warden huffed in annoyance.

“Jared! Did you seriously just interrupt my beauty sleep as well as my poetry reference to tell me about a gang rape?” He paused and thought over his words for a moment. “I know it sounds a bit harsh, but you've never warned me before. So what's the big deal this time?” 

“I was getting to that, sir. The victim of the assault is… One of our special inmates.” The Warden's eyes narrowed.

“You don't mean… JACK KNIFE?!?” The taller man gasped, raising a hand to cover his gaping mouth. 

“N-no, Sir.”

“Well, I'm out of ideas then.” The Warden shrugged.

“S-sir it's Lor… Stingray. He p-pissed off the wrong group of inmates, and they're taking revenge in the raunchiest way…”

“Pfft. Serves him right. Here in Superjail, inmates get their just deserts. And I believe Stingray’s long overdue.” The Warden crossed his arms and smiled in satisfaction. “The scales of justice are even again, my dear Jared.” For a second, he took the form of said scales, as if to prove his point.

“Warden, don't you think this is a bit… Unfair? We have taken everything away from Stingray. Without his s-suit and army, he is incredibly weak. Plus, he doesn't work out with the other inmates, and he barely eats. He's wasting away and he can't hold his own against an assault anymore. Especially against other inmates. They're b-brutes! He could easily be killed.”

“Jared, he is literally no different than our other prisoners. He'll be fine.” The Warden glanced at Jared's uneasy expression and sighed once more. “Fine. I'll go to the surveillance room and watch to make sure he survives. Just… Leave me alone. I'm sure he'll be fine anyway.” He slowly trudged to the door, opened it, then waited for Jared to leave. Once the shorter man was gone, he snapped his fingers. In a few seconds, Jailbot crashed in. “Dress.” The robot’s arms jetted out and in a flash, and the warden was clothed in his usual attire. “Okay, Jailbot. Let's go see if Stingray can beat his attackers.” The Warden leaned towards Jailbot and whispered. “Between you and me, my money's on the other inmates.”

The Warden got into the empty surveillance room just in time to see stingray be shoved to the ground and stripped from his prison uniform in a dim hallway. He fell to his knees in the remaining armor that hadn't been taken away from him when he entered the prison. Ignoring the fact that the inmates shouldn't even be out of their cells this late, he continued watching. 

“It's best not to intervene…” He muttered to himself, trying to match names with the faces of Stingray's attackers. “Best… Not to… Intervene.” He continued watching the live footage as the former villain was punched in the face, or helmet he presumed. He wasn't quite sure what it was. Instead of worrying about it, The Warden decided that enough was enough. Something inside him was irked by watching Stingray being beat up. “Fuck it, I'm going in. Wait here, Jailbot. I'll call you if I need your assistance.” He glanced at the screen again and smirked slightly. “Though maybe I'll take my time getting there.”

\---

“Listen, guys. I wasn't cheating. I swear! Would I lie to you?” Lord Stingray put on his best smile and tilted his head towards the other inmates. 

“Bitch, you've been lyin’ since you got here.” One of them grunted. Stingray's smile instantly disappeared as a fist connected with his face once again. In his weakened state, he fell to the ground. The arms of two of the three inmates grabbed his own, holding him down. The third crouched in front of him, eyeing the smaller man menacingly. Stingray took the opportunity to lash out with his high heeled boot, jabbing the inmate in the side with it. 

“Son of a bitch! These things are too much trouble. They need to go.” He began pulling Stingray's boots off, ignoring the former's attempts to get away. 

“Guys! Guys! It was just a game of poker!” Stingray screamed. “Are you dimwits really going to kill me over… What was it? A pack of cigarettes?” The inmates around him laughed almost in unison. 

“We aren't gonna kill you. Yet.” Stingray felt himself begin to tremble at the implications of the statement, watching quietly as the man pulled his boots off.

“Woah, what the fuck?” The inmate paused and looked down at the former Lord's feet. 

“There a problem, man?” One of the men holding Stingray's arms looked down at the now exposed feet. “Woah… He's yellow.”

“And he has three toes.” At that, Stingray felt the fear fade away only to be replaced with annoyance.

“I'm an alien, numbnuts. What the fuck did you expect?” He muttered, taking on an expression of disinterest. Another fist to the face shut him up quickly and caused the fear to return.

“Fuck, I thought the whole yellow thing was just the armor and a helmet… Should we still fuck him? Does he have some weird alien STDs?” The statement brought hope to Stingray, but it was crushed almost immediately.

“Eh, won't stop me. Use the prison uniform to tie him to the bars of that cell. Then we can take turns. Gimme the knife. I need to cut this… What the fuck is this uniform made of, spandex? Whatever.” The inmate held his hand out for the knife and immediately began cutting the area of Stingray's uniform that was closer to his crotch and rear. The smaller man shuddered as he felt himself slowly being exposed, then let out a sudden yelp as the knife slipped slightly and cut him. 

“BE CAREFUL YOU BLUNDERING OAF! YOU LITERAL PEICE OF SHI-” Stingray was cut off by a peice of his torn prison shirt being forced into his mouth and tied around his head. He hadn't even noticed that his hands had already been tied to the bars of the empty cell behind him.

“You're too loud.” The one cutting his uniform off spat. Finally becoming tired of cutting it off piece by piece, the inmate took a handful of the material and ripped it off with his brute strength. “Damn. You're skinny as fuck. I thought I remember you being… More muscular? And holy crap that is not a fucking dick. Is that a… Tentacle? Oh my god that's nasty.” The action had exposed Stingray's stomach, crotch, and chest, and finally feeling hopeless, he began to cry. “Whatever.” The inmate watched his victim’s tears falling from desperate eyes, but only sneered in return. The other two chuckled. Wordlessly, the first one put down the knife and spread Stingray's thighs to nudge a dry finger towards his entrance. In his restraints, Stingray thrashed violently in a final attempt to get away. As hard as he tried, his attempts were futile. A single inmate alone was stronger than him now, so three could restrain him easily. He felt the finger continue to push on, a slight pain accumulating. Quickly, however, it pulled out. Stingray sighed in relief. 

“He's too tight,” The inmate between his legs chuckled. “he might be a virgin. But with the guys around here, probably not.” He smiled darkly. “I need to prep him a bit.” The inmate looked down. “I'm doing this for my pleasure, not yours. Bitch.” He then proceeded to spit in his hand and on his fingers and brought themback between Stingray's legs. He pushed in again with no hesitation and began thrusting his finger in and out. After only a second, he pushed in a second one, causing Stingray to whimper in a disgusting mix of pain and slight pleasure. As the thrusting continued, a slight moan escaped his throat and fought it's way past the shirt in his mouth.

“Holy shit, he's getting off on this!” A voice from behind him chuckled. “What a good little bitch. Hurry up and fuck him so I can have my turn.” 

Suddenly, the fingers were pulled out and Stingray watched as the first inmate unzipped his pants and revealed his fairly large cock. He spat in his hand again and pumped his already throbbing member a couple of times, only to thrust it in suddenly without warning.

“A-ah!” Stingray involuntarily moaned through the shirt and arched his back. It hurt terribly due to the lack of proper preparation, but he felt a bit of pleasure with it. He felt more tears fall messily as the man pulled out and thrust back in again repeatedly, the pace he set immediately harsh and fast. He only paused to adjust his position, which lead to Stingray's prostate being hammered by the thick cock. By this point, the smaller man was nearly cross-eyed and drooling through the shirt.

The thrusting continued for several minutes before they became faster and more sporadic, and Stingray felt his insides being filled with thick, warm cum. He shuddered in disgust and hoped that the man was clean. Just as he thought it was over, the first inmate pulled out and he noticed the two holding his arms playing rock, paper, scissors. The one that won switched places with the one that had just finished and immediately unzipped his pants. He thrust in almost immediately, apparently ignoring the cum leaking out of Stingray's abused asshole. 

\---

By the end of the third inmate’s turn, Stingray had come three times and was shaking from overstimulation. It was at that time that the Warden decided to reveal himself to the group. Stingray was too dazed to notice, but the three inmates backed up a bit.

“Well, well, well. Gentlemen. It appears you've been having yourselves…” The Warden paused and glanced down at the shaking form on the ground. “a good time…”

“Man, fuck off, Warden.” The tallest of the inmates growled. “I don't wanna have to kick your ass too. But I will.” He stepped forward, but The Warden wagged his finger. 

“Ah, ah, ah.” The suited man seemingly disappeared and reappeared behind the group. “Can't we all get along and be friends? I mean, it certainly looks like you're suuuuuper friendly with him.” He pointed at Stingray, who had finally come to and looked up at him pitifully. 

“That's it.” One of the inmates tried to throw a punch, but was interrupted.

“Jailbot!” The robot suddenly burst through the wall and immediately grabbed all the inmates in his robotic arms. Three more arms sprung out and impaled the inmates, gripped their spines, and ripped them out of their bodies in true Superjail style. The Warden seemed completely unfazed, and stood there smiling. After a moment, he looked at Stingray. 

“Hm. Jailbot, you can go. I'll escort Stingray to his cell and ensure he gets cleaned up.” The murderous robot seemed unsure for a moment, but did as it was told. Once they were alone, The Warden spoke. 

“You look like you've had a rough time, huh?” He glanced at the man on the floor, who was avoiding eye contact. It was hard for The Warden not to stare at Stingray's exposed backside, which was still leaking. “Well, let's get you… Untied.” He leaned down and untied the shirt from his mouth, expecting he'd have plenty of things to say. Instead, Stingray stayed quiet, still refusing to look The Warden in the eye. He watched in silence as his hands were untied from the cell bars and he was pulled to his feet. He stumbled a bit, falling on The Warden, who held him up. 

“Jeez, Jared was right. You have let yourself go. You're so thin…” Stingray finally looked him in the eye and sneered. 

“Shut up.” He limped past The Warden, picked up his boots, and started making his way towards the showers. “I'm going to go clean myself. Thanks for the help, now leave me the fuck alone.” The Warden stopped him, putting a hand on his shoulder. 

“It's late and you can't be unsupervised. I'll have to watch you.” At Stingray's look of disgust, he continued. “Unless you want me to go get Alice to come watch you. But she gets cranky when she's woken up…”

“Ugh. Fine.” They continued walking, or in Stingray's case, limping, to the showers. Both decided it was best to ignore the elephant in the room, and just stay silent.

Once they got to the showers, Stingray set his boots down and began taking off the remainder of his torn uniform. The black spandex fell in a small, limp pile on the floor. The Warden watched in silence as the shower was turned on, and Stingray began to wash himself. It was only when he noticed something odd that he spoke.

“You shower with your helmet on?” Stingray sighed in return.

“It's not a helmet. It's not my face either, but it is permanently fixed to my body. It doesn't come off.” He muttered curtly. 

“Interesting…” They continued on in silence until Stingray got around to washing his backside. He cringed at how sticky it was, and how the cum of three people was still slowly leaking out of him. He carefully began fingering himself to get all of the cum out, wincing at the pain remaining from overstimulation and being fucked relentlessly. The Warden bit his lip, feeling his member growing hard as Stingray seemingly forgot he was there and began releasing breathy little moans. 

After a moment of this, Stingray stopped, apparently happy with his cleanliness. The Warden, however, had subconsciously stepped forward until he was standing behind the slightly smaller man. As Stingray turned the shower off and turned around, his eyes widened as he saw The Warden standing there. 

“Woah, you're unreasonably close. If you'd kindly back the fuck up, that'd be great.” Stingray sneered, wrapping a towel around himself in a very feminine fashion. The Warden only stepped forward. 

“I want… To fuck you.” He stated in a monotone voice.

“Well that escalated quickly. Is this your idea of a joke, Warden?” The slightly taller man shook his head.

“I saw what they did to you. I want to try my hand at it.”

“You're kidding.” Stingray frowned, watching as the Warden's expression remained the same. “You're not kidding. U-uh, that's not a good idea… Look at me. I'm yellow, I'm an alien to you. A tyrannical ruler!” He backed up against the prison wall, raising a hand in defense. 

“That doesn't matter to me. I mean, look. I'm a magical fucking prison warden. With, what? Magical powers? I dunno, canon’s a bitch to guess at.” The Warden shrugged, smirking at Stingray's confusion towards his statement.

“Just leave me alone. I've had enough of this shit today.” The former lord’s voice was weak and pitiful. “Ever since I let myself become weak, stuff like this is a regular thing. I'm an easy target. Today, I was especially unlucky and they found out I was cheating at poker night.”

“Hm… I think I have an offer for you, Stingray.” 

“What is it?” He questioned, suddenly perking up.

“If you become my, to put it simply, sex toy, I will offer you protection.” The Warden smiled in a predatory manner, which was very unusual given his personality. 

“I… I can't. I’d be the laughing stock of the prison if anyone found out I'm your little pet.”

“Well, Stingray, I never mentioned pet-play, but if that's what you're into… Each to their own, I guess.” The Warden teased. “How about I make the deal a little better…” 

“…I'm listening…”

“I will give you your own cell. No cellmate. And I'll allow you to occasionally sleep in my quarters. Plus… I won't make you eat the cafeteria food. From now on, it will be any edible food you want.” 

“Hm…” Stingray frowned. All of this was very uncharacteristic of The Warden. “I have one question.”

“And that is?”

“Why are you doing this? What is compelling you to… Take me?”

“Oh, that's easy. Running Superjail is a lonesome job. I only have Alice, Jailbot, and Jared as true companions.” He sighed, feigning distraught. Then, despite them being the only two in the room, he leaned in and whispered. “Plus my hand just isn't doing it for me anymore. I haven't gotten laid since the first time we ran into The Mistress.”

“Ech.” Stingray adopted a look of disgust. “TMI, Warden.” He paused, reconsidering the offer. “So, you want my body in exchange for my own protection?”

“That sounds about right.”

“And you can guarantee I'll be safe?”

“I'll program Jailbot to be at your beck and call in case of an emergency.”

“…Deal.” He extended a hand for The Warden to shake. “When should I first report to your bedroom to-?” He was cut off by The Warden grabbing his hand and pulling him to his chest. 

“I think I'll accept my first payment right now. After all,” He batted his eyes, “Nothing is more romantic than shower sex.” 

“U-uh…”

“C’mon, Stingy Wingy, I'll make you feel good.” 

“If you ever call me that again, I will literally rip your throat out.”

“Kinky.”

“UGH.” Stingray blushed angrily, flipping The Warden off. 

“This relationship is already off to a great start. Now, come on. Take the towel off. I probably don't even need to prep you right now if you're still loose.”

“How come you get to top?” Stingray whined.

“Because, you're the sex toy in this relationship. Besides, you're already prepped.”

“But I'm sore! And I just recovered from the overstimulation! Plus I still have some dignity.”

“Yeah, I don't think so. Do you want my protection and food?”

“...Yes.”

“Then get up against the wall and brace yourself.” Stingray obeyed, taking the towel from his hips and turning to face the wall. He put his hands against it and bent over slightly. He shuddered as he heard the sound of a zipper behind him. Almost immediately after, he felt the head of The Warden's member pressing against his already sore hole. 

“Don't worry, I'll be a little gentler than those other guys.”

“Okay… I'm not sure how long I'll last… I'm still recovering from… Y'know.”

“Yeah, yeah.” The Warden suddenly thrusted in, causing Stingray to let out a pleasure filled yelp. A medium pace was set, the sound of skin slapping and breathy moans filling the area. The Warden smirked as Stingray's knees wobbled, his body threatening to give out and fall to the ground. Not wanting the fun to end so soon, the Warden pulled out and picked the trembling yellow form up. He turned him around and pressed his back against the wall before pushing back in and beginning to thrust once more. Stingray threw his head back and wrapped his legs around the Warden's waist.

“Warden…” Stingray gasped, his eyes closed. His body shuddered and his back rubbed against the wall with each thrust. He reached a clawed hand between their bodies and began jerking himself off furiously, his inhuman cock curling and wrapping around his hand. The Warden looked down between them and stopped thrusting as he saw something he hadn't noticed before. He closed his eyes and sighed. 

“Dear god please tell me you don't have a fucking tentacle where your dick should be.”

“I TOLD YOU I'M AN ALIEN TO YOU. I'M NOT INCLINED TO HAVE A PENIS, EXCUUUUUSE ME.” Stingray groaned and The Warden shook his head and shrugged before picking up the pace again.

“Whatever. But you're never topping with that.” Stingray rolled his eyes, then began jerking himself off again. Warden shifted himself, which resulted in Stingray letting out a loud moan as the Warden's cock struck just right inside of him. 

“A-aah, W-warden! There! I'm coming!” The Warden suddenly pulled out and let the former lord fall to the ground. “H-hey!” 

“As much as I'd love to see your blushing face as you cum for the fourth time tonight, my fun is just beginning.” He took Stingray's hand and zipped his pants up, his still-hard cock visible in the front. “Jailbot!” He yelled in the empty shower room, his voice echoing. At first, it seemed like nothing happened. But not a second later, Jailbot burst in, only to stop with a look of horror of his screen at the sight of a very naked, very erect, Stingray. “To my bedroom, please.” Jailbot hesitated before complying, grabbing both individuals with one long appendage. “Hold on tight!” Warden winked at Stingray, who only looked away in disgust and embarrassment. They burst out of the roof of the showers and through several floors of the jail before finally, and seemingly magically, ending up in Warden's quarters. “Leave us, Jailbot.” Jailbot let out a few confused beeps in return. “I said, leave us.” The robot looked a bit sad, but left immediately.

“Nice pad.” Stingray muttered, although it sounded sarcastic at best. 

“Let's get down to business.” Warden had a maniacal grin on his face, causing Stingray to worry about what was to come. “I'll be trying several things out on you. Not all tonight, but definitely within our little… Relationship.”

“What kind of ‘things,’ if you don't mind me asking? Because honestly that just sounds terrifying.” 

“Oh, y'know. Different kinks, techniques, positions.” Warden shrugged nonchalantly. “Nothing too scary. All I ask for is your complete obedience. From now on, you belong to me. In return, you get protection, food, and… Special treatment. But you must keep it a secret from other prisoners. I don't want word getting out.”

“Trust me, neither do I.” Stingray muttered.

“For now, let's go vanilla. A.K.A., I pound you into the mattress.” 

“I… Oh.” Stingray blushed. “You're very… Upfront about these things, aren't you? I thought I was bad…”

“I have no shame. Also, before we begin again, I must warn you. Our relationship will be purely sexual. None of that nasty feelings crap. Got it?” 

“Ew.” Stingray stuck his long tongue out in disgust. “Don't have to tell me twice.” 

“Good!” Warden leaned in and whispered in an attempt to be sexy. “Now get on the bed. On your knees, ass up.”

Stingray nearly gagged at the thought of what he was agreeing to, and flipped Warden off before complying. He crawled onto the large bed, marvelling at the soft mattress and plush bedding. He stuck his ass in the air, nearly jumping as he immediately felt the mattress dip behind him. As if it couldn't get any worse, he felt a warm breath on his rear, causing him to actually jump. The Warden's tongue began prodding at his entrance, licking circles around it. 

“F-fuck. What are you doing? That's disgusting!” Stingray whimpered as the wet muscle dipped in, and out again. The Warden soon began tongue-fucking him, causing him to practically melt into the mattress. Despite his earlier complaint, he whined when the Warden pulled away. 

“Very good…” Warden smiled and licked his lips, pulling his cock out again. He leaned forward and pushed himself into Stingray quickly, while he was still recovering from his puddle-like state. The latter's eyes widened at the sudden intrusion. “I'm not holding back this time, ‘Lord.’” Warden smirked and began thrusting at a brutal speed, practically shoving Stingray's face in the mattress with each thrust. 

“F-fuck! I'm going to…” Stingray was cut off by a particularly hard thrust that simultaneously smashed his face into the mattress and made him cum. Despite his release, Warden continued pounding into him, causing him to shake with overstimulation. “Hurry up!” Stingray snapped, trying not to let his voice waver. 

“You're in no position to give orders, pet.” The Warden growled dangerously. Despite that, his thrusts were becoming slightly sporadic. He thrust in, once, twice, three times, and came with a groan. Stingray whimpered as he felt warm cum fill his insides for the fourth time that night. 

“Ugh… That was terrible…” Stingray looked utterly fucked out and defeated. 

“Gee, that's a confidence booster for my sexual performance.” Warden rolled his eyes and pulled out. He nudged Stingray’s side, signaling for him to roll over and onto his back. He complied immediately, cum dripping out of him with the movement. The Warden looked down in disgust. “Ugh. There is no way I'm going to let you ruin my sheets with both of our cum.”

“What’re you going to do? Kick me out? After what I've been through tonight, I can handle that blow to my conscience.” Stingray growled, looking defensive and tired at the same time. The Warden looked at him for a moment, thinking. 

“Wait right here.” He immediately sauntered off to the bathroom, leaving Stingray to his own devices. Stingray's first instinct was to run while the Warden wasn't there. But after a moment of thought, he decided that there was nothing the Warden could do to him that would be worse than what he'd already been through. And the possibility of a soft bed tempted him to stay. So, instead of running, he closed his eyes, falling asleep almost immediately.

“Here we go- Oh. Asleep already.” The Warden emerged from the bathroom with a washcloth, smiling slightly at the sleeping villain. Silently, he moved forward and began gently cleaning Stingray's lower regions. When he was done, he crawled into the bed and wrapped himself around Stingray, who shifted slightly in his sleep. 

“This looks like the start to something great…”

**Author's Note:**

> Might make continuations. Comment if you want more.


End file.
